The Mosher Method in the Study of Natural Products
Author(s):
- Charalambos MichaelPhD Candidate, Deparment of ChemistryNorth Carolina State UniversityEmail: [email protected]More by Charalambos Michael
- Mark W. RuszczyckyResearch Engineering/Scientist Associate III, College of Pharmacy UT AustinEmail: [email protected]More by Mark W. Ruszczycky
- Wei-chen ChangProfessor, LORD Corporation Distinguished Scholar, Department of ChemistryNorth Carolina State UniversityEmail: [email protected]More by Wei-chen Chang
Publication Date:
February 6, 2026
Copyright ©
2026 American Chemical Society
eISBN:
9780841295803
DOI:
10.1021/acsinfocus.7e9022
Read Time:
two to three hours
Collection:
5
Publisher:
American Chemical Society
The structural complexity and diversity of natural products have made their study an incredibly rich and interesting field with applications in the pharmaceutical, agrochemical, and biotechnology industries. But that structural complexity and diversity also pose significant challenges. One of the most important yet difficult challenges is assigning absolute stereochemical configurations, which can be vital to the biological activity of a natural product and the pharmacological properties of a medicine.
This primer introduces the popular Mosher ester method for determining the stereochemical configurations of secondary alcohols and primary amines bound to a secondary carbon. An introduction to stereochemistry and its importance to the study of natural products is provided, followed by a detailed description of the chemical principles behind the Mosher analysis. Practical aspects of the methodology are also described to provide a starting point for investigators looking to put the technique into practice in a real experimental setting.
Several case studies from the structural analysis of natural products, highlighting different aspects of the Mosher method, are discussed, offering a walk-through of the synthetic methodology, application, and data interpretation. Several such examples have also been selected to demonstrate how the technique can be applied and extended in novel and interesting ways.
By the end of this primer, the reader will not only have a broader understanding of stereochemical analysis but also gain the knowledge necessary to synthesize Mosher esters, apply the derivatization method effectively, and interpret the resulting NMR data to deduce absolute configurations. The reader is encouraged to work through the initial examples in detail and then test their understanding with the case studies presented in the latter sections.
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Detailed Table of Contents
About the Series
Preface
Chapter 1
Stereochemistry
1.1
Stereoisomerism
1.2
Stereochemical Configurations
1.3
Stereoisomerism in Biology
1.4
That’s a Wrap
1.5
Read These Next
Chapter 2
The Mosher Method
2.1
Theory
2.1.1
Mandelate Esters
2.1.2
MTPA Esters
2.1.3
MTPA Amides
2.2
Derivatization
2.2.1
Use of Acyl Chlorides
2.2.2
Use of Carbodiimide Coupling Reagents
2.2.3
Troubleshooting
2.3
That’s a Wrap
2.4
Read These Next
Chapter 3
Case Studies
3.1
Introductory Examples
3.1.1
Lavanduquinocin
3.1.2
Stasorbicillinoid B
3.1.3
Laurefurenynes
3.2
Further Examples
3.2.1
Caveamide B
3.2.2
Caylobolide A
3.2.3
Plakortides
3.3
Conclusions
3.4
That’s a Wrap
3.5
Read These Next
Bibliography
Glossary
Index
Reviewer quotes
Chiral chemistry is a complex yet important topic. This is a good primer, or refresher, regarding nomenclature and biological ramifications, and a seminal method of structure elucidation. As a pharmaceutical biologist working in the field for many years, especially with natural products, this primer was a good reminder of the critical importance of chirality, as well as an inspiration as to how colleagues working in this field, as chemists, have the genius of sorting out these important structural features.
A concise and accessible digital primer that highlights the significance of Mosher’s method in natural products. The content provides valuable insights that can aid in structural elucidation and enhance the understanding of stereochemical aspects in this field. It serves both as an introduction and as a practical reference for researchers in this field.
A concise, accessible and up-to-date introduction to the Mosher method. It balances technical precision with clarity, offers useful examples and figures, and provides both theoretical context and practical tips. The content provides a clear, comprehensive yet digestible overview of the Mosher method, combining theory, derivatization strategies and real examples that highlight key knowledge. After reading it, I gained a better understanding of how stereochemistry assignments are made in practice, why they are important, and which experimental considerations matter most. The selected case studies are particularly valuable in demonstrating practical problem-solving and analysis strategies.
Charalambos Michael is a graduate student in the Department of Chemistry at North Carolina State University. He received his BS in chemistry from the University of Cyprus in 2022. His current work lies at the interface of chemistry and biology, focusing on the chemoenzymatic synthesis of bioactive natural products and the elucidation of enzymatic mechanisms under the mentorship of Prof. Wei-chen Chang. His research is directed towards mastering the techniques of organic synthesis and biocatalysis with the goal of developing an integrated approach to novel synthetic strategies for natural products.
Mark W. Ruszczycky earned his bachelor’s degree in biochemistry and master’s degree in chemistry from the University of California, Riverside. He was subsequently admitted to the Medical Scientist Training Program at the Case Western Reserve University School of Medicine in Cleveland, Ohio, where he earned his MD and PhD under the guidance of Vernon E. Anderson. Mark then joined the laboratory of Hung-wen Liu in the Division of Chemical Biology and Medicinal Chemistry in the College of Pharmacy at the University of Texas, Austin, where he continues to study the chemistry of enzyme catalyzed reactions in the biosynthesis of natural products.
Wei-chen Chang earned his bachelor’s degree in agricultural chemistry in 2003 from National Taiwan University under the supervision of Tien-Yau Luh. After a two year mandatory military service, he pursued his PhD in the Medicinal Chemistry Program of the School of Pharmacy at the University of Texas at Austin under the guidance of Hung-wen (Ben) Liu. Wei-chen then joined the laboratory of Marty Bollinger and Carsten Krebs at Pennsylvania State University. He then started his independent career at North Carolina State University, where his group studies the chemistry of enzyme catalyzed reactions in the biosynthesis of natural products as well as enzyme catalysis and engineering.
